2,2-Dimethyl-propionic acid (R)-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl ester | 196861-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-propionic acid (R)-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl ester
• 英文别名: [(3R)-3-[tert-butyl(dimethyl)silyl]oxy-4-oxobutyl] 2,2-dimethylpropanoate
• CAS: 196861-58-2
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: XNJQXQZVFAXGTR-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (R)-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl ester 在 4-二甲氨基吡啶 、 四氧化锇 、 正丁基锂 、 N-甲基吲哚酮 、 sodium amalgam 、 4-甲基苯磺酸吡啶 、 乙酸酐 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.25h， 生成 (3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-{(2S,3R,5S)-3-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-methoxy-tetrahydro-furan-2-yl}-4-methoxy-butan-1-ol
  参考文献：
  名称：

  螺旋霉素糖苷配基的全合成

  摘要：

  借助Kishi-Nozaki-Takai偶联反应，碘醛β- 8f已有效地转化为标题糖苷配基。

  DOI：

  10.1016/s0040-4039(97)10758-4
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (R)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-butyl ester 在 palladium on activated charcoal 草酰氯 、 氢气 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~25.0 ℃ 、100.0 kPa 条件下， 反应 7.0h， 生成 2,2-Dimethyl-propionic acid (R)-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl ester
  参考文献：
  名称：

  Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments

  摘要：

  Acetalisation of p-anisaldehyde by either (R) or (S)-butanetriol has been shown to occur selectively and quantitatively by using Noyori's protocol. The crystalline dioxane derivatives R-6a and S-ba which formed respectively, in these conditions have been convened efficiently into the title fragments of spiramycin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01523-2

文献信息

• Toward a total synthesis of an aglycone of spiramycin; installation of the hydroxy groups at C-4 and C-5: a model study
  作者：G Oddon、D Uguen、A De Cian、J Fischer

  DOI：10.1016/s0040-4039(97)10760-2

  日期：1998.3

  The stereochemical course of the osmium-mediated bis-hydroxylation of the allylic derivative 6c, whose the structure is closely related to that of a C-1/C-7 fragment of the title aglycone, has been established unambiguously by X-ray analysis of a carboxylic acid derived from one of the two diastereomeric dials which formed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments
  作者：P. Breuilles、G. Oddon、D. Uguen

  DOI：10.1016/s0040-4039(97)01523-2

  日期：1997.9

  Acetalisation of p-anisaldehyde by either (R) or (S)-butanetriol has been shown to occur selectively and quantitatively by using Noyori's protocol. The crystalline dioxane derivatives R-6a and S-ba which formed respectively, in these conditions have been convened efficiently into the title fragments of spiramycin. (C) 1997 Elsevier Science Ltd.
• Total synthesis of an aglycone of spiramycin
  作者：G Oddon、D Uguen

  DOI：10.1016/s0040-4039(97)10758-4

  日期：1998.3

  The iodoaldehyde β-8f has been converted efficiently into the title aglycone by means of the Kishi-Nozaki-Takai coupling reaction.

  借助Kishi-Nozaki-Takai偶联反应，碘醛β- 8f已有效地转化为标题糖苷配基。